Ink jet ink composition

ABSTRACT

An ink jet ink composition contains a disperse dye, and a compound represented by the following formula (1): 
     
       
         
         
             
             
         
       
     
     In the formula, Ar 1  and Ar 2  each independently represent an aryl group; R 1  and R 2  each independently represent a chemical species selected from the group consisting of hydrogen, alkyl groups having a carbon number of 1 to 3, a sulfo group, —O—SO 3 H, a carboxy group, and a hydroxy group; and n&#39;s each independently represent an integer of 0 to 5. The content of the compound represented by formula (1) is 0.1% by mass to 20% by mass relative to the total mass of the ink jet ink composition.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a continuation of U.S. patent application Ser. No.15/714,075, filed on Sep. 25, 2017, which claims priority to JapanesePatent Application No. 2017-112297, filed on Jun. 7, 2017 and JapanesePatent Application No. 2016-194422, filed on Sep. 30, 2016. The entiredisclosures of the above applications are hereby expressly incorporatedby reference herein.

BACKGROUND 1. Technical Field

The present invention relates to an ink jet ink composition.

2. Related Art

Known disperse dye inks contain low-polarity dye fine crystals ofseveral tens of nanometers to less than one micrometer in diameter thatis dispersed in an aqueous liquid by using a dispersant and/or asurfactant. A dispersant or a surfactant is essential to keep a dispersedye suspended in a medium (solvent) without settling and thus to controlthe viscosity and the surface tension to be appropriate as an ink (See,for example, JP-A-10-298477).

Although the disperse dye, which is pulverized into fine crystals beforebeing dispersed, is intrinsically insoluble in water and similarsolvents, it has been confirmed that the disperse dye can dissolve at amolecular level in the presence of a solvent, a dispersant, and asurfactant (that is, dissolve in an ink composition). In addition, thesaturation solubility of a coloring material in an ink depends ontemperature. If the solvent temperature is reduced, the saturationsolubility of the coloring material decreases, and the amount of thecoloring material corresponding to the temperature differenceprecipitates out of the ink, accordingly. The composition of ink ischanged by evaporation of low-boiling-point components in the vicinityof ink jet nozzles, and the coloring material cannot be kept dispersedor suspended, forming aggregates of foreign matter.

The state of a disperse dye dispersion is easily affected by disturbanceand compositional changes in the ink. It is known that, in pale colorinks prepared by simply diluting a deep color without changing theproportion of the disperse dye to the dispersant, the state of thedispersion of the disperse dye is not easily maintained. It is desiredto minutely adjust the composition of the ink, including the proportionof the dispersant and the disperse dye. Particularly for pale colorinks, it has been found that it is not necessarily effective, inmaintaining the state of the dispersion of the disperse dye, to add thedispersant with a higher content than the disperse dye, because anexcess of the dispersant dissolves the disperse dye and produces foreignmatter from the disperse dye, or the portion of the dispersant that hasnot been involved in dispersing the disperse dye turns into foreignmatter.

SUMMARY

An advantage of some aspects of the invention is that it provides an inkjet ink composition in which foreign matter derived components thereinis reduced.

The present inventors have conducted intensive research to solve theabove issues and found that the issues can be solved by using a specificcompound.

According to an aspect of the invention, there is provided an ink jetink composition containing a disperse dye, and a compound represented bythe following formula (1):

In the formula, Ar₁ and Ar₂ each independently represent an aryl group;R₁ and R₂ each independently represent a chemical species selected fromthe group consisting of hydrogen, alkyl groups having a carbon number of1 to 3, a sulfo group, —O—SO₃H, a carboxy group, and a hydroxy group;and n's each independently represent an integer of 0 to 5. In the inkcomposition, foreign matter derived from components of the ink isreduced.

Preferably, the proportion of the compound represented by formula (1) inthe ink jet ink composition is 0.01 part by mass to 150 parts by massrelative to 1 part by mass of the disperse dye. Preferably, the ink jetink composition further contains a dispersant. Preferably, theproportion of the total mass of the disperse dye and the compoundrepresented by formula (1) is in the range of 0.24 to 4.0 relative tothe mass of the dispersant. Preferably, the proportion of the compoundrepresented by formula (1) is 0.001 part by mass to 1000 parts by massrelative to 1 part by mass of the dispersant. Preferably, the dispersantcontains a formalin condensate of an aromatic sulfonic acid compound.Preferably, the molecule of the disperse dye has a condensed ringstructure.

DESCRIPTION OF EXEMPLARY EMBODIMENTS

Embodiments of the invention will now be described. However, theinvention is not limited to the disclosed embodiments, and variousmodifications may be made without departing from the scope and spirit ofthe invention.

Ink Jet Ink Composition

An ink jet ink composition according to an embodiment of the inventioncontains a disperse dye and a compound represented by the followingformula (1):

In the formula, Ar₁ and Ar₂ each independently represent an aryl group;R₁ and R₂ each independently represent a chemical species selected fromthe group consisting of hydrogen, alkyl groups having a carbon number of1 to 3, a sulfo group, —O—SO₃H, a carboxy group, and a hydroxy group;and n's each independently represent an integer of 0 to 5.

Known dispersants for disperse dyes include naphthalenesulfonic acid,formalin condensate thereof, and ligninsulfonic acid. These dispersantsare, in general, materials having a high molecular weight, produced bysulfonating a fossil fuel compound, such as naphthalene, anthracene, orphenanthrene and further condensing the sulfonated compound withformalin for polynuclearization, or by sulfonating lignin derived fromwood or pulp. The coloring material content in pale color inks is lowerthan that in deep color inks. Accordingly, in the pale color ink, allthe dispersant, which is intended to enclose the coloring material, doesnot necessarily enclose the coloring material, and an excess thereofremains in the liquid. Such an excess dispersant is a cause of foreignmatter produced in the ink jet ink composition during storage.

On the other hand, in the present embodiment, a compound that is similarto the disperse dye and represented by formula (1) is added to the inkjet ink composition. This compound acts as an alternative to thedisperse dye and is enclosed by the dispersant.

The compound of formula (1) has a sulfonyl bis dimer structure formed bydimerizing one or two aromatic compounds with a sulfonyl group. In thiscompound, the groups derived from the aromatic compounds are compatiblewith the disperse dye, while the sulfonyl group is compatible with thedispersant having a highly polar substituent. In general, a disperse dyeinsoluble in aqueous solvents and a dispersant having a highly polarsubstituent, such as a sulfo group, so as to disperse the disperse dyehave a large difference in polarity. The compound represented by formula(1) can reduce such a polarity difference and increase the affinity orcompatibility between the disperse dye and the dispersant.

Consequently, the dispersibility of the disperse dye is increased, andthe excess dispersant is reduced. In addition, the compound representedby formula (1) is also satisfactorily dispersed. Thus, the presentembodiment reduces occurrence of foreign matter from ink components. Thephrase “foreign matter (derived) from ink components” used herein refersto foreign matter derived from the disperse dye, foreign matter derivedfrom the compound represented by formula (1), and foreign matter derivedfrom the dispersant.

Disperse Dye

The ink composition of the present embodiment contains a disperse dye.The disperse dye is a compound suitably used as a dye to colorhydrophobic synthetic fiber, such as polyester, nylon, or acetate, andis insoluble or poorly soluble in water.

Disperse dyes are cited as follows.

Yellow disperse dyes include, but are not limited to, C. I. DisperseYellows 3, 4, 5, 7, 9, 13, 23, 24, 30, 33, 34, 42, 44, 49, 50, 51, 54,56, 58, 60, 63, 64, 66, 68, 71, 74, 76, 79, 82, 83, 85, 86, 88, 90, 91,93, 98, 99, 100, 104, 108, 114, 116, 118, 119, 122, 124, 126, 135, 140,141, 149, 160, 162, 163, 164, 165, 179, 180, 182, 183, 184, 186, 192,198, 199, 202, 204, 210, 211, 215, 216, 218, 224, 227, 231, and 232.

Orange disperse dyes include, but are not limited to, C. I. DisperseOranges 1, 3, 5, 7, 11, 13, 17, 20, 21, 25, 29, 30, 31, 32, 33, 37, 38,42, 43, 44, 45, 46, 47, 48, 49, 50, 53, 54, 55, 56, 57, 58, 59, 61, 66,71, 73, 76, 78, 80, 89, 90, 91, 93, 96, 97, 119, 127, 130, 139, and 142.

Red disperse dyes include, but are not limited to, C. I. Disperse Reds1, 4, 5, 7, 11, 12, 13, 15, 17, 27, 43, 44, 50, 52, 53, 54, 55, 56, 58,59, 60, 65, 72, 73, 74, 75, 76, 78, 81, 82, 86, 88, 90, 91, 92, 93, 96,103, 105, 106, 107, 108, 110, 111, 113, 117, 118, 121, 122, 126, 127,128, 131, 132, 134, 135, 137, 143, 145, 146, 151, 152, 153, 154, 157,159, 164, 167, 169, 177, 179, 181, 183, 184, 185, 188, 189, 190, 191,192, 200, 201, 202, 203, 205, 206, 207, 210, 221, 224, 225, 227, 229,239, 240, 257, 258, 277, 278, 279, 281, 288, 298, 302, 303, 310, 311,312, 320, 324, and 328.

Violet disperse dyes include, but are not limited to, C. I. DisperseViolets 1, 4, 8, 23, 26, 27, 28, 31, 33, 35, 36, 38, 40, 43, 46, 48, 50,51, 52, 56, 57, 59, 61, 63, 69, and 77.

An example of green disperse dyes may be, but is not limited to, C. I.Disperse Green 9.

Brown disperse dyes include, but are not limited to, C. I. DisperseBrown 1, 2, 4, 9, 13, and 19.

Blue disperse dyes include, but are not limited to, C. I. Disperse Blues3, 7, 9, 14, 16, 19, 20, 26, 27, 35, 43, 44, 54, 55, 56, 58, 60, 62, 64,71, 72, 73, 75, 79, 81, 82, 83, 87, 91, 93, 94, 95, 96, 102, 106, 108,112, 113, 115, 118, 120, 122, 125, 128, 130, 139, 141, 142, 143, 146,148, 149, 153, 154, 158, 165, 167, 171, 173, 174, 176, 181, 183, 185,186, 187, 189, 197, 198, 200, 201, 205, 207, 211, 214, 224, 225, 257,259, 267, 268, 270, 284, 285, 287, 288, 291, 293, 295, 297, 301, 315,330, and 333.

Black disperse dyes include, but are not limited to, C. I. DisperseBlacks 1, 3, 10, and 24.

Those disperse dyes may be used singly or in combination.

In the present embodiment, disperse dyes having a molecular weight of380 or less are preferred. The molecular weight of such a disperse dyeis preferably 340 or less, more preferably in the range of 270 to 340,and still more preferably in the range of 280 to 340. The use of adisperse dye having a molecular weight of 380 or less increases thetransfer efficiency of the ink when used in a sublimation transfersystem or the like.

Examples of the disperse dye having a molecular weight of 380 or lessinclude C. I. Disperse Reds 11, 53, 55, 59, 60, and 191; C. I. DisperseYellows 3, 7, 8, 23, 39, 51, 54, 60, 71, and 163; C. I. Disperse Oranges1, 20, and 25; C. I. Disperse Blues 19, 26, 56, 72, 81, and 359; and C.I. Disperse Violets 8, 17, 27, and 28. These disperse dyes may be usedsingly or in combination.

Among these, preferred are C. I. Disperse Reds 60 and 191, C. I.Disperse Blue 359, and other disperse dyes having an anthraquinoneskeleton containing a hydrophilic group, such as amino or hydroxy. Thesedyes tend to be compatible with the compound represented by formula (1).

Preferably, the molecule of the disperse dye has a condensed ringstructure of naphthalene, anthracene, phenanthrene, or a derivativethereof. For example, C. I. Disperse Red 60 is represented by thefollowing formula:

As shown in this formula, the compound represented by formula (1) issimilar to disperse dyes having a condensed ring structure in terms ofpolarity and molecular structure, and, accordingly, can reduceoccurrence of foreign matter from ink components.

The disperse dye content is preferably 0.1% by mass to 12% by mass, morepreferably 1% by mass to 10% by mass, and still more preferably 2% bymass to 5% by mass, relative to the total mass of the ink jet inkcomposition. The term “pale color ink” mentioned herein refers to thathaving a total disperse dye content of 5% by mass or less. The term“deep color ink” mentioned herein refers to that having a total dispersedye content of more than 5% by mass. The ink jet ink composition of thepresent embodiment may be a pale color ink or a deep color ink.

Compound Represented by Formula (1)

The compound represented by formula (1) is dispersed in the same manneras the disperse dye by the dispersant without affecting the color of theprinted article. The use of such a compound reduces foreign matterresulting from the excess dispersant and increases the affinity orcompatibility between the disperse dye and the dispersant, thusimproving the stability of the dispersion.

In formula (1), Ar₁ and Ar₂ each represent an aryl group, and examplesthereof include, but are not limited to, phenyl, naphthyl, anthracenyl,and phenanthrenyl. Phenyl, naphthyl, and anthracenyl are advantageous.Preferably, Ar₁ and Ar₂ are the same aryl group.

R₁ and R₂ each may represent an alkyl group, and examples of the alkylgroup include, but are not limited to, methyl, ethyl, n-propyl,isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, n-pentyl, neopentyl,n-hexyl, n-heptyl, and n-octyl. Alkyl groups having a carbon number of 1to 3, particularly, methyl and ethyl, are advantageous.

Examples of the compound represented by formula (1) include (but are notlimited to):

The content of the compound represented by formula (1) is preferably0.1% by mass to 20% by mass, more preferably 1% by mass to 15% by mass,and still more preferably 2% by mass to 10% by mass, relative to thetotal mass of the ink jet ink composition. When the content of thecompound of formula (1) is 0.1% by mass or more, foreign matterresulting from the excess dispersant tends to decrease, and the affinityor compatibility between the disperse dye and the dispersant tends toincrease to improve the stability of the dispersion. When the content ofthe compound of formula (1) is 20% by mass or less, the compound islikely to be sufficiently dispersed by the dispersant. The compound isthus unlikely to remain undispersed and is therefore unlikely to act asforeign matter.

The proportion of the total content of the disperse dye and the compoundof formula (1) to the content of the dispersant, that is, (dispersedye+compound of formula (1))/dispersant), is preferably in the range of0.24 to 4.0, more preferably in the range of 0.5 to 2.4, and still morepreferably in the range of 1.0 to 3.0. When the proportion of theseconstituents is in such a range, foreign matter resulting from theexcess dispersant tends to decrease, and the affinity or compatibilitybetween the disperse dye and the dispersant tends to increase to improvethe stability of the dispersion.

The proportion of the compound represented by formula (1) is preferably0.01 part by mass to 150 parts by mass, more preferably 0.2 part by massto 5 parts by mass, and still more preferably 0.5 part by mass to 1.5parts by mass, relative to 1 part by mass of the disperse dye. When theproportion of the compound of formula (1) to the disperse dye is 0.01part by mass or more, foreign matter resulting from the excessdispersant tends to decrease, and the affinity or compatibility betweenthe disperse dye and the dispersant tends to increase to improve thestability of the dispersion. When the proportion of the compound offormula (1) to the disperse dye is 100 parts by mass or less, thecompound is likely to be sufficiently dispersed by the dispersant. Thecompound is thus unlikely to remain undispersed and is thereforeunlikely to act as foreign matter.

The compound of formula (1) may be synthesized by any process withoutparticular limitation, and, for example, by dimerizing one or twoaromatic compounds with a sulfonyl group. More specifically, sulfuricacid is added to one or two aromatic compounds that will form the aryldomains of the formula (1) to produce a compound having a sulfonyl bisdimer structure.

Dispersant

The ink jet ink composition of the present embodiment may contain adispersant. The dispersant may be, but is not limited to, an anionicdispersant, a nonionic dispersant, a polymer dispersant. Anionicdispersants are preferred.

Exemplary anionic dispersants include formalin condensates of alkylnaphthalenesulfonic acids, such as formalin condensate of creosote oilsulfonic acid, formalin condensate of cresol sulfonic acid, formalincondensate of phenolsulfonic acid, formalin condensate ofβ-naphtholsulfonic acid, formalin condensate ofmethylnaphthalenesulfonic acid, and formalin condensate ofbutylnaphthalenesulfonic acid; and formalin condensate of a mixture ofβ-naphthalenesulfonic acid and β-naphtholsulfonic acid, formalincondensate of a mixture of cresol sulfonic acid and2-naphthol-6-sulfonic acid, and formalin condensate of ligninsulfonicacid. Formalin condensates of aromatic sulfonic acids are preferred.

Examples of the nonionic dispersant include, but are not limited to,ethylene oxide adducts of phytosterol and ethylene oxide adducts ofcholestanol.

Examples of the polymer dispersant include, but are not limited to,partially alkyl-esterified polyacrylic acid, polyalkylene polyamine,polyacrylic acid salts, styrene-acrylic acid copolymer, and vinylnaphthalene-maleic acid copolymer.

The dispersant content is preferably 0.1% by mass to 20% by mass, morepreferably 1% by mass to 15% by mass, and still more preferably 2% bymass to 10% by mass, relative to the total mass of the ink jet inkcomposition. When the dispersant content is 0.1% by mass or more, thedisperse dye can be more stably dispersed. When the dispersant contentis 20% by mass or less, foreign matter resulting from the excessdispersant tends to decrease.

The proportion of the compound represented by formula (1) is preferably0.001 part by mass to 1000 parts by mass, more preferably 0.1 part bymass to 5 parts by mass, and still more preferably 0.2 part by mass to 1part by mass, relative to 1 part by mass of the dispersant. When theproportion of the compound of formula (1) to the dispersant is 0.001part by mass or more, foreign matter resulting from the excessdispersant tends to decrease, and the affinity or compatibility betweenthe disperse dye and the dispersant tends to increase to improve thestability of the dispersion. When the proportion of the compound offormula (1) to the dispersant is 1000 parts by mass or less, thecompound is likely to be sufficiently dispersed by the dispersant. Thecompound is thus unlikely to remain undispersed and is thereforeunlikely to act as foreign matter.

Surfactant

The surfactant may be, but is not limited to, a nonionic, surfactant, acationic surfactant, or an anionic surfactant. Nonionic surfactants arepreferred. By using a nonionic surfactant, ejection stability tends tobe improved.

Exemplary nonionic surfactants include, but are not limited to,acetylene glycol-based surfactants, silicone surfactants,polyoxyethylene alkyl ether-based surfactants, polyoxypropylene alkylether-based surfactants, polycyclic phenyl ether-based surfactants,sorbitan derivatives, and fluorosurfactants. Among these, acetyleneglycol-based surfactants, silicone surfactants, and fluorosurfactantsare preferred. Silicone surfactants are more preferred.

Acetylene glycol-based surfactants are superior to the other nonionicsurfactants in terms of the ability of appropriately controlling thesurface tension and the interface tension, and have the nature of hardlyfoaming. Acetylene glycol-based surfactants have good affinity(wettability) to ink supply channels and are, accordingly, suitableparticularly as cleaning solution.

The acetylene glycol-based surfactant used in the present embodiment maybe, but is not limited to, at least one selected from the groupconsisting of 2,4,7,9-tetramethyl-5-decyne-4,7-diol and alkylene oxideadducts thereof, and 2,4-dimethyl-5-decyne-4-ol and alkylene oxideadducts thereof. The acetylene glycol-based surfactant is commerciallyavailable, and examples thereof include, but are not limited to, Olfine104 series and Olfine E series, such as Olfine E1010 (each a product ofAir Products and Chemicals Inc.); and Surfynol 465 and Surfynol 61 (eacha product of Nissin Chemical Industry). Acetylene glycol-basedsurfactants may be used singly or in combination.

Exemplary fluorosurfactants include, but are not limited to,perfluoroalkylsulfonic acid salts, perfluoroalkylcarboxylic acid salts,perfluoroalkylphosphoric acid esters, perfluoroalkylethylene oxideadducts, perfluoroalkylbetaines, and perfluoroalkylamine oxidecompounds. Fluorosurfactants are commercially available, and examplesthereof include, but are not limited to, S-144 and S-145 (each producedby Asahi Glass); FC-170C, FC-430, and Fluorad-FC4430 (each produced bySumitomo 3M); FSO, FSO-100, FSN, FSN-100, and FS-300 (each produced byDupont); and FT-250 and FT-251 (each produced by Neos).Fluorosurfactants may be used singly or in combination.

The silicone surfactant used in the present embodiment may be apolysiloxane compound or a polyether-modified organosiloxane. Thesilicone surfactant is commercially available, and examples thereofinclude, but are not limited to, BYK-306, BYK-307, BYK-333, BYK-341,BYK-345, BYK-346, BYK-347, BYK-348, and BYK-349 (each produced by BYK);and KF-351A, KF-352A, KF-353, KF-354L, KF-355A, KF-615A, KF-945, KF-640,KF-642, KF-643, KF-6020, X-22-4515, KF-6011, KF-6012, KF-6015, andKF-6017 (each produced by Shin-Etsu Chemical).

The surfactant content is preferably 0.1% by mass to 5% by mass, morepreferably 0.1% by mass to 2% by mass, and still more preferably 0.2% bymass to 1% by mass, relative to the total mass of the ink jet inkcomposition.

Solvent

Preferably, the ink jet ink composition of the present embodimentfurther contains a solvent. The solvent may be, but is not limited to,an organic solvent or water.

Water

The ink jet ink composition of the present embodiment may contain water.The water may be pure water or ultra-pure water from which ionicimpurities have been removed as much as possible. Examples of such waterinclude ion exchanged water, ultrafiltered water, reverse osmosis water,and distilled water. The use of sterile water prepared by, for example,UV irradiation or addition of hydrogen peroxide can reduce theoccurrence of mold or bacteria in the ink stored for a long time. Thewater content in the ink jet ink composition is preferably 50% by massto 95% by mass, more preferably 60% by mass to 90% by mass, and stillmore preferably 70% by mass to 80% by mass, relative to the total massof the ink composition.

Organic Solvent

The ink jet ink composition of the present embodiment may contain anorganic solvent.

Examples of the organic solvent include, but are not limited to,glycerin, ethylene glycol, diethylene glycol, triethylene glycol,propylene glycol, dipropylene glycol, 1,3-propanediol, 1,2-butanediol,1,2-pentanediol, 1,2-hexanediol, 1,4-butanediol, 1,5-pentanediol,1,6-hexanediol, diethylene glycol mono-n-propyl ether, ethylene glycolmono-isopropyl ether, diethylene glycol mono-isopropyl ether, ethyleneglycol mono-n-butyl ether, ethylene glycol mono-t-butyl ether,diethylene glycol mono-n-butyl ether, triethylene glycol monobutylether, diethylene glycol mono-t-butyl ether, propylene glycol monomethylether, propylene glycol monoethyl ether, propylene glycol mono-t-butylether, propylene glycol mono-n-propyl ether, propylene glycolmonoisopropyl ether, propylene glycol mono-n-butyl ether, dipropyleneglycol mono-n-butyl ether, dipropylene glycol mono-n-propyl ether,dipropylene glycol monoisopropyl ether, diethylene glycol dimethylether, diethylene glycol diethyl ether, diethylene glycol dibutyl ether,diethylene glycol ethyl methyl ether, diethylene glycol butyl methylether, triethylene glycol dimethyl ether, tetraethylene glycol dimethylether, dipropylene glycol dimethyl ether, dipropylene glycol diethylether, tripropylene glycol dimethyl ether, methanol, ethanol, n-propylalcohol, isopropyl alcohol, n-butanol, 2-butanol, tert-butanol,isobutanol, n-pentanol, 2-pentanol, 3-pentanol, tert-pentanol, and otheralcohols and glycols; and N,N-dimethylformamide, N,N-dimethylacetamide,2-pyrrolidone, N-methyl-2-pyrrolidone, 2-oxazolidone,1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, sulfolane, and1,1,3,3-tetramethyl urea. These organic solvents may be used singly orin combination.

The organic solvent content is preferably 1% by mass to 25% by mass,more preferably 5% by mass to 20% by mass, and still more preferably 10%by mass to 20% by mass, relative to the total mass of the ink jet inkcomposition.

Other Ingredients

The ink jet ink composition of the present embodiment may furthercontain, if necessary, one or more of the additives generally used ininks, such as a fungicide, a preservative, an antioxidant, anultraviolet absorbent, a chelating agent, an oxygen absorbent, a pHadjuster (such as triethanolamine, adipic acid, or tris buffer), and asolubilizing agent. These additional ingredients may be used singly orin combination.

EXAMPLES

The invention will be further described in detail with reference toExamples and Comparative Examples. However, the invention is not limitedto the following Examples.

Ingredients of Ink Compositions

The following compounds were major materials used in the inkcompositions of the Examples and Comparative Examples.

Coloring Material

DR 60: C. I. Disperse Red 60

DY 54: C. I. Disperse Yellow 54

DBl 359: C. I. Disperse Blue 359

DR 191: C. I. Disperse Red 191

DY 163: C. I. Disperse Yellow 163

DBl 165: C. I. Disperse Blue 165

Dispersant

NS: Sodium naphthalenesulfonate formalin condensate LAVELIN AN-40(produced by Dai-ichi Kogyo Seiyaku)

Surfactant

BYK 348: Silicone surfactant produced by BYK

Organic Solvent

Gly: Glycerin

TEGMME: Triethylene glycol monomethyl ether

Synthesis of Compound 1

Into the mixture of 1 mol of benzene and 1 mol of benzenesulfonic acidwas added 3 mol of sulfuric acid, and the resulting mixture wassubjected to a reaction at 150° C. for about 5 hours. Then, calciumcarbonate in an amount corresponding to the moles of the added water andsulfuric acid was added for neutralization, followed by rinsing withwater. Then, the reaction system was allowed to stand at 0.5 atmosphereand 150° C. for evaporation of unreacted components and excess water toyield the following compound 1:

Synthesis of Compound 2

Into 1 mol of naphthalene was added 3 mol of sulfuric acid, and themixture was subjected to a reaction at 150° C. for about 5 hours. Then,calcium carbonate in an amount corresponding to the moles of the addedwater and sulfuric acid was added for neutralization, followed byrinsing with water. Then, the reaction system was allowed to stand at0.5 atmosphere and 150° C. for evaporation of unreacted components andexcess water to yield the following compound 2:

Synthesis of Compound 3

Into the mixture of 1 mol of anthracene and 1 mol of methylanthracenewas added 3 mol of sulfuric acid, and the mixture was subjected to areaction at 150° C. for about 5 hours. Then, calcium carbonate in anamount corresponding to the moles of the added water and sulfuric acidwas added for neutralization, followed by rinsing with water. Then, thereaction system was allowed to stand at 0.5 atmosphere and 150° C. forevaporation of unreacted components and excess water to yield thefollowing compound 3:

Synthesis of Compound 4

Compound 4 represented by the following formula (1′) where R₁ and R₂ areeach a SO₃H group was synthesized in the same manner as compound 2,except that 1 mol of naphthalene was replaced with 1 mol ofnaphthalenesulfonic acid.

Synthesis of Compounds 5A

Compounds 5A represented by the following formula where R₁ and R₂ areeach the corresponding functional group shown in Table 4 or 5 weresynthesized in the same manner as compound 2, except that 1 mol ofnaphthalene, methylnaphthalene, naphthalenesulfonic acid,—OSO₃H-substituted naphthalene, naphthalenecarboxylic acid, or naphtholwas used as the aromatic compound.

Synthesis of Compound 5B

Compound 5B represented by the following formula where R₁ and R₂ areeach the functional group shown in Table 5 was synthesized in the samemanner as compound 2, except that 1 mol of naphthalenesulfonic acid wasused as the aromatic compound.

Synthesis of Compound 5C

Compound 5C represented by the following formula where R₁ and R₂ areeach the functional group shown in Table 5 was synthesized in the samemanner as compound 2, except that 1 mol of naphthalenesulfonic acid wasused as the aromatic compound.

Preparation of Ink Compositions

Ingredients were mixed with the proportions shown in Tables 1 to 4 andfully stirred. Each of the ink compositions was thus prepared. Thevalues in Tables 1 to 4 are on a percent-by-mass basis, and the totalcontent of each composition is 100.0% by mass.

TABLE 1 Formula (1) Coloring compound (B) Dispersant material (A)Compound Compound Compound (C) Surfactant DR60 DY54 DBI359 1 2 3 NSBYK348 Example 1 3 — — 3   — — 6 0.5 Example 2 3 — — — 3   — 6 0.5Example 3 3 — — — — 3   6 0.5 Example 4 1 0.5 1 2.5 — — 5 0.5 Example 51 0.5 1 — 2.5 — 5 0.5 Example 6 1 0.5 1 — — 2.5 5 0.5 Comparative 3 — —— — — 6 0.5 Example 1 Comparative 1 0.5 1 — — — 5 0.5 Example 2 OrganicForeign solvent Proportion matter Gly TEGMME Water Total (A + B)/C B/AB/C rating Example 1 10 3 Balance 100 1.00 1.00 0.500 A Example 2 10 3Balance 100 1.00 1.00 0.500 A Example 3 10 3 Balance 100 1.00 1.00 0.500A Example 4 10 3 Balance 100 1.00 1.00 0.500 A Example 5 10 3 Balance100 1.00 1.00 0.500 A Example 6 10 3 Balance 100 1.00 1.00 0.500 AComparative 10 3 Balance 100 — 0 0 E Example 1 Comparative 10 3 Balance100 — 0 0 E Example 2

TABLE 2 Formula (1) Coloring compound (B) Dispersant material (A)Compound Compound Compound (C) DR191 DY163 DBI165 1 2 3 NS Example 7 3 —— 3   — — 6 Example 8 3 — — — 3   — 6 Example 9 3 — — — — 3   6 Example10 1 0.5 1 2.5 — — 5 Example 11 1 0.5 1 — 2.5 — 5 Example 12 1 0.5 1 — —2.5 5 Comparative 3 — — — — — 6 Example 3 Comparative 1 0.5 1 — — — 5Example 4 Organic Foreign Surfactant solvent Proportion matter BYK348Gly TEGMME Water Total (A + B)/C B/A B/C rating Example 7 0.5 10 3Balance 100 1.00 1.00 0.500 A Example 8 0.5 10 3 Balance 100 1.00 1.000.500 A Example 9 0.5 10 3 Balance 100 1.00 1.00 0.500 A Example 10 0.510 3 Balance 100 1.00 1.00 0.500 A Example 11 0.5 10 3 Balance 100 1.001.00 0.500 A Example 12 0.5 10 3 Balance 100 1.00 1.00 0.500 AComparative 0.5 10 3 Balance 100 — 0 0 E Example 3 Comparative 0.5 10 3Balance 100 — 0 0 E Example 4

TABLE 3 Formula (1) Coloring compound (B) Dispersant Organic Foreignmaterial (A) Compound 4 (C) Surfactant solvent Proportion matter DR60(R₁═R₂═SO₃H) NS BYK348 Gly TEGMME Water Total (A + B)/C B/A B/C ratingExample 13 0.1 0.1 0.1 0.5 10 3 Balance 100 2.00 1.00 1.000 A Example 140.1 1 1 0.5 10 3 Balance 100 1.10 10.00 1.000 A Example 15 0.1 10 10 0.510 3 Balance 100 1.01 100.00 1.000 A Example 16 0.1 15 15 0.5 10 3Balance 100 1.01 150.00 1.000 A Example 17 0.1 0.1 5 0.5 10 3 Balance100 0.04 1.00 0.020 C Example 18 0.1 1 5 0.5 10 3 Balance 100 0.22 10.000.200 C Example 19 0.1 10 5 0.5 10 3 Balance 100 2.02 100.00 2.000 AExample 20 0.1 15 5 0.5 10 3 Balance 100 3.02 150.00 3.000 B Example 211 0.1 0.1 0.5 10 3 Balance 100 11.00 0.10 1.000 C Example 22 1 1 1 0.510 3 Balance 100 2.00 1.00 1.000 A Example 23 1 10 10 0.5 10 3 Balance100 1.10 10.00 1.000 A Example 24 1 15 15 0.5 10 3 Balance 100 1.0715.00 1.000 A Example 25 1 0.1 5 0.5 10 3 Balance 100 0.22 0.10 0.020 CExample 26 1 1 5 0.5 10 3 Balance 100 0.40 1.00 0.200 B Example 27 1 105 0.5 10 3 Balance 100 2.20 10.00 2.000 A Example 28 1 15 5 0.5 10 3Balance 100 3.20 15.00 3.000 B Example 29 1 10 1 0.5 10 3 Balance 10011.00 10.00 10.000 B Example 30 10 0.1 0.1 0.5 10 3 Balance 100 101.000.01 1,000 C Example 31 10 1 1 0.5 10 3 Balance 100 11.00 0.10 1,000 CExample 32 10 10 10 0.5 10 3 Balance 100 2.00 1.00 1,000 A Example 33 1015 15 0.5 10 3 Balance 100 1.67 1.50 1,000 B Example 34 10 0.1 5 0.5 103 Balance 100 2.02 0.01 0.020 C Example 35 10 1 5 0.5 10 3 Balance 1002.20 0.10 0.200 C Example 36 10 10 5 0.5 10 3 Balance 100 4.00 1.002.000 C Example 37 10 15 5 0.5 10 3 Balance 100 5.00 1.50 3.000 CExample 38 10 10 1 0.5 10 3 Balance 100 20.00 1.00 10.000 C Example 3910 1 10 0.5 10 3 Balance 100 1.10 0.10 0.100 A Example 40 10 10 20 0.510 3 Balance 100 1.00 1.00 0.500 A Comparative 0.1 — 15 0.5 10 3 Balance100 — — — E Example 5 Comparative 1 — 15 0.5 10 3 Balance 100 — — — EExample 6

TABLE 4 Coloring Formula (1) Dispersant Organic Foreign material (A)compound (B) (C) Surfactant solvent Proportion matter DR60 Compound 5ANS BYK348 Gly TEGMME Water Total (A + B)/C B/A B/C rating Example 41 R₁═5 5 10 0.5 10 3 Balance 100 1.00 1.00 0.500 A Example 42 R₂═ 5 10 10 0.510 3 Balance 100 1.50 2.00 1.000 B Example 43 H 5 20 10 0.5 10 3 Balance100 2.50 4.00 2.000 C Example 44 R₁═ 5 5 10 0.5 10 3 Balance 100 1.001.00 0.500 A Example 45 R₂═ 5 10 10 0.5 10 3 Balance 100 1.50 2.00 1.000B Example 46 CH₃ 5 20 10 0.5 10 3 Balance 100 2.50 4.00 2.000 C Example47 R₁═ 5 5 10 0.5 10 3 Balance 100 1.00 1.00 0.500 A Example 48 R₂═ 5 1010 0.5 10 3 Balance 100 1.50 2.00 1.000 A Example 49 SO₃H 5 20 10 0.5 103 Balance 100 2.50 4.00 2.000 B Example 50 R₁═ 5 5 10 0.5 10 3 Balance100 1.00 1.00 0.500 A Example 51 R₂═ 5 10 10 0.5 10 3 Balance 100 1.502.00 1.000 A Example 52 OSO₃H 5 20 10 0.5 10 3 Balance 100 2.50 4.002.000 B Example 53 R₁═ 5 5 10 0.5 10 3 Balance 100 1.00 1.00 0.500 AExample 54 R₂═ 5 10 10 0.5 10 3 Balance 100 1.50 2.00 1.000 A Example 55COOH 5 20 10 0.5 10 3 Balance 100 2.50 4.00 2.000 B Example 56 R₁═ 5 510 0.5 10 3 Balance 100 1.00 1.00 0.500 A Example 57 R₂═ 5 10 10 0.5 103 Balance 100 1.50 2.00 1.000 A Example 58 OH 5 20 10 0.5 10 3 Balance100 2.50 4.00 2.000 C

TABLE 5 Formula (1) Coloring compound (B) Dispersant material (A)Compound Compound Compound (C) Surfactant DR60 5A 5B 5C NS BYK348Example 59 R₁═ 5 3 3 3 10 0.5 Example 60 R₂═ 5 5 3 1 10 0.5 Example 61SO₃H 5 3 1 5 10 0.5 Example 62 5 1 5 3 10 0.5 Example 63 5 5 4 — 10 0.5Example 64 5 4 — 5 10 0.5 Example 65 5 — 5 4 10 0.5 Organic Foreignsolvent Proportion matter Gly TEGMME Water Total (A + B)/C B/A B/Crating Example 59 R₁═ 10 3 Balance 100 1.40 1.80 0.900 A Example 60 R₂═10 3 Balance 100 1.40 1.80 0.900 A Example 61 SO₃H 10 3 Balance 100 1.401.80 0.900 A Example 62 10 3 Balance 101 1.40 1.80 0.900 A Example 63 103 Balance 102 1.40 1.80 0.900 A Example 64 10 3 Balance 102 1.40 1.800.900 A Example 65 10 3 Balance 102 1.40 1.80 0.900 A

Checking for Foreign Matter

The ink compositions, each of 30 mL in volume, were enclosed inrespective test ink packs so as to avoid entrance of air, and the testink packs were allowed to stand at 60° C. for 5 days. Then, 10 mL eachof the ink compositions was filtered through a metal mesh filter (poresize: 10 μm), and the number of pieces of foreign matter on the metalmesh filter per 1 mm square was counted. The resulting number of piecesof foreign matter was rated according to the following criteria:

A: The number of pieces of crystalline foreign matter was 0 per 1 mmsquare.

B: The number of pieces of crystalline foreign matter was 1 to 5 per 1mm square.

C: The number of pieces of crystalline foreign matter was 6 to 25 per 1mm square.

D: The number of pieces of crystalline foreign matter was 26 to 50 per 1mm square.

E: The number of pieces of crystalline foreign matter was 51 or more per1 mm square.

What is claimed is:
 1. An ink jet ink composition comprising: a dispersedye; and a compound represented by the following formula (1):

wherein Ar₁ and Ar₂ each independently represent an aryl group, R₁ andR₂ each independently represent a chemical species selected from thegroup consisting of hydrogen, alkyl groups having a carbon number of 1to 3, a sulfo group, —O—SO₃H, a carboxy group, and a hydroxy group, andn's each independently represent an integer of 0 to 5, wherein thecontent of the compound represented by formula (1) is 0.1% by mass to20% by mass relative to the total mass of the ink jet ink composition.2. The ink jet ink composition according to claim 1, wherein theproportion of the compound represented by formula (1) relative to 1 partby mass of the disperse dye is 0.01 part by mass to 150 parts by mass.3. The ink jet ink composition according to claim 1, further comprisinga dispersant.
 4. The ink jet ink composition according to claim 3,wherein the proportion of the total mass of the disperse dye and thecompound represented by formula (1) is in the range of 0.24 to 4.0relative to the mass of the dispersant.
 5. The ink jet ink compositionaccording to claim 3, wherein the proportion of the compound representedby formula (1) relative to 1 part by mass of the dispersant is 0.001part by mass to 1000 parts by mass.
 6. The ink jet ink compositionaccording to claim 3, wherein the dispersant contains a formalincondensate of an aromatic sulfonic acid compound.
 7. The ink jet inkcomposition according to claim 1, wherein the molecule of the dispersedye has a condensed ring structure.